Our search for “CEO shoes” started with a Christmas card left out on the dining table. The holiday flier was what you would expect — smiling family members, a few notes on their year, some kid achievements — but as my husband leaned in to look at the photo, what really caught his eye was the extraordinarily sharp dress shoes our friend was wearing. They had this well-worn, classy, effortless cool that wasn’t overly stuffy and didn’t scream “I’m wearing these for the family photo.”
Turns out the pair in question were the Craftsman boots by Australian company R.M. Williams, which cost $590. After some research, we discovered the brand has a bit of a cult following — Cillian Murphy was spotted wearing to its boots and even Wirecutter praises the brand’s style and longevity. And despite the steep price tag, wearers — including the CEO in the Christmas card, who admitted to owning 10 pairs from the brand — swear that the boots are a smart buy, adding that even after years of use they’ll find a shoe cobbler to fix any issues before buying cheaper alternatives.
But purchasing a pair of shoes, even ones that are likely worth the investment, for $500+ dollars is a big ask in today’s economy. So if you’re looking for similar pairs for considerably less, below are 11 pairs of alternatives to the high-end buy that are well-reviewed and more-budget friendly.
An inexpensive lookalike with over 10,000 reviews and 4.6 stars on Amazon
These Bruno Marc Chelsea boots have over 16,000 reviews on Amazon and a solid 4.5 star ranking. They might not be made using premium leather (they come in vegan leather or suede) and lack the same sort of design quality as the R.M. William's pair, but they are very well-reviewed and buyers and lauded for their longevity despite being under $50. The shoes come in several different colors and in choices for either vegan leather and suede, elastic panels to easily slide into, EVA midsoles for extra padding and comfort and a slight lift with a 0.98-inch heel. And with so many customers raving about not only the look and comfort of these Chelsea boots you can splurge and buy a few pairs to add guilt-free versatility into your wardrobe.
The shoes are available in seven neutral colors and in sizes 6.5-15 in men's at Amazon.
Promising review: "Still in excellent condition after years of wear. I have owned these suede Chelsea boots since 2019 and they are still in excellent condition. They have been worn to weddings church and date nights and continue to look great. The suede has held up very well with no major signs of wear and the boots have maintained their shape over time. They are comfortable enough to wear for extended periods and polished enough to dress up. I honestly did not realize how long I have owned them until recently which says a lot about the quality. If there had been durability issues I would remember it. Overall these have proven to be a reliable well made pair of boots that have stood the test of time." — Sam
A stylish seasonal buy
If you're after R.M. Williams' Turnout boot (which costs $619), you might be interested in this Amazon find, which offers a similar silhouette for under $100. The latter is unlikely to have the same sort of multi-year staying power as the higher-end pick, but with over 400 reviews and 4.4 stars they offer a smart and more economical choice for a season or two. Most reviewers warned the shoes run about a half a size too large, and several mentioned adding cushioned insoles for added comfort, but overall the reviews are positive.
The shoes are available in sizes 8-13 in men's at Amazon.
Promising review: "The boots were awesome made out of great material super comfy to were just a half size bigger I'm for the most part a size 9.5 but for these the width was to big so I'll have to get a size 9 though that's just me every one is different and other wise a dope item a must purchase if your trying to get your money's worth without breaking your wallet or getting something cheap." — Christopher Gama
A sleek and functional pair designed to slip on easily
These Marc Joseph New York ankle boots come in several colors, almost all of which are on sale at Zappos right now. The boots are designed with technology, meaning they are easy to slip on without struggling with flimsy togs or laces — a rarity for a pair of Chelsea-style boots. The shoes have side gore panels, a gel heel insert and thickly padded footbed — so they're designed to be comfortable to walk in and durable for street wear with double-density rubber outsoles.
The shoes are available in sizes 7-14 in men's at Zappos.
Promising Review: "The best Chelsea Boot I have ever owned!! I don't even need to bend down or touch the boots to put them on, simply step in and go, incredible! The quality and conform on these are amazing." — Zappos reviewer
A mid-priced pair with unique stitching
These full-grain leather boots come in at a not-totally-cheap — but also not eye-popping — price point, making them a good compromise for folks interested in something that's going to last a few years without having to shell out as much as you would for a PlayStation. They're lined with nappa — a leather that’s known for its softness — and equipped with a stippled rubber outsole for added traction. Reviewers say they fit "very comfortably."
Fans of this mid-priced brand can also get the Reeve in a zippered style at Nordstrom.
Two (slightly more) affordable options from a household-name heritage brand
Like R.M. Williams, Barbour also has a bit of cult following due to its long history and reputation for quality. But Barbour isn't a Australian line — it's a British heritage brand founded in 1894, a fifth-generation family owned business that continues to produce their line in the UK. The line is well-known for their waxed coats, but their bags and shoes have a similar following from buyers willing to pay extra for the brand's quality.
At $220, the Farsley boot is still a splurge, but way more affordable than its Aussie counterparts.
Another option with a distinct design is the Barbour Hadston chukka boot, which comes in three different colors and sizes 7-13 at Bloomingdale’s
A CEO-worthy pair from a brand people are obsessed with
The Quince leather dress Chelsea boot has a more narrow and pointed toe give off a sophisticated and decidedly not outdoorsy look. They look high-end, but cost less than half of what the R.M. Williams' boots sell for. And there are three color options in black, charcoal and chestnut. The boots are made with a smooth calfskin leather or suede depending on color selection, are lined with leather and have a foot friendly Ortholite footbed cushions. And despite looking like the shoes are office or date only, they also have a leather outsole with a durable rubber heel tap for walking.
The shoes are available in sizes 7-13 in men's at Quince.
Promising review: "The boot I needed. I really like this boot. It's clean and simple. For me it's understated and just what I was looking for. The raw leather sole means I don't have to worry about it being slippery the way some new shoes are when they arrive. The top leather is quality and it seems like it will protect my feet from water. I just need to shine them and I'll be ready to go." — FancyB.
A CEO-worth cowboy boot
As a true Texas native, I can confirm that not enough people know that cowboy boots can be worn in the board room. Tecovas' classic Warren boots are handcrafted in León, Mexico and designed in Austin, and inspire a similar loyalty as R.M. Williams (despite the former being a much newer brand). Sure, the cowboy silhouette might be a far cry from the Chelsea, but they’re still sported by CEOs and on in-the-know shoehounds alike.
The shoes are available in sizes 7 to 15 in men's at Tecovas.
Promising review: "Love them. Comfortable right out of the box and clearly well made. After just a few wears, I’m impressed with the quality, and I’ve gotten compliments every time I’ve had them on. Tecovas did a great job with these." — Scott W.
Another iconic brand and their trusted Chelsea boot
J.Crew's Kenton Chelsea boot is a close twin to the more expensive R.M. Williams pair. The boots are made with a premium leather, solid Vibram soles, craftsman stitching and are available in black or brown. Fans of these shoes do warn that they run a smidge small, so ordering half a size up would be wise. And frequent reviewers also recommended waiting to buy a pair once they go on sale, since J.Crew tends to have pretty significant seasonal discounts, which can be worth the wait.
The shoes are available in a black or rust brown color and in sizes 7-13 in men's at J.Crew.
Promising review: "Perfect Chelsea Boots. Great quality leather and rubber sole for the price. Some break-in needed to be comfortable. I bought both colors and have received many compliments!" — Scholar10